A.N. Once again, sorry for the delay. It took me a while to write and then I had to wait for my beta starzee to work her magic! Hope you enjoy!
The next morning, at the family brunch at the penthouse, Dan was recounting the previous night's double date with Nate and Mandy.
"I don't understand," Dan said, leaning back in his chair, "she's perfect for Nate. She's age-appropriate, she's smart and knows all about politics, she's classy and pretty... They have so much in common! When I talk to her sometimes I feel like I'm speaking to Nate!"
"It can be boring dating someone who has the same personality and the same interests as you," Rufus explained.
Dan shook his head. "I'm sure they're not that similar. I mean, you need common interests to start building a connection, right? Jenny, you know Nate, what do you think?" He asked curiously.
Jenny had been trying to ignore Dan all morning, but he made it impossible. He had somehow made it his mission to find Nate a girlfriend and Jenny was finding it hard to watch his attempts at matchmaking, knowing that at any moment Nate might find one of these girls attractive and decide to start dating her.
"I don't know, Dan," she answered somewhat dryly, "maybe he just doesn't want to date anyone right now. Besides, he's perfectly capable of finding someone by himself." She just wanted the conversation over right now.
"I don't think so. I mean, first there was you, and then there was that married woman, what was her name? And then he dated Bree... and that was a disaster of epic proportions. And do I even need to mention Juliet?" he asked and Jenny was a little pissed that he included her in that list.
"I should get started on my designs for the play," Jenny said as she got up. Apparently Dan wasn't going to shut up anytime soon. "May I be excused?" she asked Lily.
"Of course, sweetheart," Lily said in a compassionate tone, knowing how difficult this whole conversation must be for her.
Lily and Serena exchanged a knowing look as Jenny left the table. As she walked to her room, Jenny heard a smack.
"What? What did I do this time?" She heard Dan ask, annoyed.
A few weeks later, Nate found Jenny in her room, sitting at her desk with three piles of paper in front of her.
"Hey, you're early!" Jenny said happily as she rose to greet him.
"Yeah, I thought we'd grab a bite to eat before the movie. What are you doing?" He walked over to the desk where he saw three college acceptance letters: The Marangoni Fashion School in Milan, the Esmod France Fashion School in Paris and the Parsons New School of Design in New York. Nate whistled. "Jenny, you got into all three?" he asked proudly.
Jenny nodded. "I got into two more, but these are my final choices."
"Congratulations." Did it only sound forced to him? He hoped so.
Jenny sighed and sat on her bed. She waited until Nate joined her to start speaking. "I just don't know if I want to go away for that long. Did you ever regret staying in Manhattan and going to Columbia?" she asked with wide innocent eyes.
"No, but that was me. Going to Columbia was different from what my family wanted, so that's how I asserted myself. You can't base your decision on my experience," he said to her though it killed him to do it.
Jenny laid her head on Nate's shoulder, finding some comfort in his presence. She wasn't anywhere near close to a decision, but she still had a few weeks to figure it out and in the meantime, the movie would be a good distraction.
Nate took a deep breath before the doors of the elevator opened to Chuck's penthouse suite. Jenny hadn't made her decision about college yet and it was getting harder and harder being around her without blurting out that he wanted her to stay. So when Chuck offered to hang out that day he took him up on it.
"I half-expected you not to show up," Chuck said from behind the bar.
"I know, I'm sorry I haven't been around," Nate said. Their friendship was obviously still strained but Nate figured he wouldn't be able to repair it unless they actually spent time together. He did kind of miss Chuck since they'd been friends for such a long time.
They played pool and drank for a while, but their easy camaraderie was gone and they both knew it. They both drank more than usual and when Nate missed two easy shots in a row he decided it was time to quit. He walked over to the couch and dropped heavily on the cushions with a sigh.
"I thought you were over it," Chuck said softly while looking out the window.
"What are you talking about?" Nate asked. He took another sip from his drink.
"I slept with Jenny. I thought you'd forgiven me for that. You said you did," Chuck said in an accusing tone.
"I don't want to talk about this," Nate said as a warning.
"Well, we have to. Because I don't see what else could be the problem, here." Chuck turned around to face his friend but Nate kept looking down at his glass.
"I slept with Jenny," Chuck continued when Nate didn't speak, "because she was upset and I thought I had just lost Blair," he explained.
"You had no right," Nate growled.
"I didn't know she was a virgin, she didn't tell me that!" Chuck practically yelled back.
"It should have been me!" Nate yelled, getting up suddenly. "I should have been her first," he declared in a quieter voice. He'd screwed up in so many ways with Jenny and the fact that she'd gone to Chuck for comfort was a testament to that. He felt so much guilt over that as you can only lose your virginity once and she would have to live with the fact hers was lost to Chuck and not him. He wanted it to be him!
"So you're not mad at me," Chuck said, trying to understand as he walked toward the couch and sat down. "You're mad at yourself."
Nate sighed, nodded, and joined him.
"Are you in love with her?" Chuck raised an eyebrow.
Nate nodded again, not trusting his voice.
"Then what are you waiting for? You have a chance to fix things and be together, why don't you take it?" Chuck asked in confusion. Everyone knew that Jenny was in love with Nate. He didn't see the issue.
"She's going off to college," Nate said, "she has her whole life in front of her. I don't want to hold her back," he explained.
It was Chuck's turn to sigh. "Blair and I were holding each other back; in the end that's why we broke up. We wanted a chance to see who we could be as individuals because we consumed each other too much when we were together. But I see now, the more time we spend apart the more we grow in different directions. And I have less and less faith that we'll ever find our way back to each other." He paused. "Don't let that happen to you and Jenny," Chuck said sincerely. Nate was sure it was possibly the best advice Chuck had ever given him.
Nate took a sip, contemplating what Chuck said. He truly believed in timing, that if two people were at different points in their lives then the chances of them having a successful relationship was slim at best. He and Jenny had never been closer than right now, had never been so in synch with each other, even though she was two years younger than him and still in high school.
"Alright, I'll do it. I'll tell Jenny I'm in love with her," he declared with a smile. It was as if a weight had been lifted off his shoulders until he wondered... how was he going to tell her?